4-Amino-3-(o-tolyl-oxymeth-yl)-1H-1,2,4-triazole-5(4H)-thione.

The asymmetric unit of the title compound, C(10)H(12)N(4)OS, contains two independent mol-ecules, A and B, which differ significantly in the relative orientations of the benzene and triazole rings. The dihedral angle between the above two rings is 6.94 (5)° in mol-ecule A and 77.60 (5)° in mol-ecule B. In the crystal, mol-ecules are linked into a three-dimensional network by N-H⋯S, N-H⋯O, N-H⋯N and C-H⋯S hydrogen bonds and π-π inter-actions between the benzene and triazole rings [centroid-centroid distance = 3.5311 (6) Å] are also present.

Related literature

For the pharmaceutical activity of triazole derivatives, see: Amir et al. (2008 ▶); Kuş et al. (2008 ▶); Padmavathi et al. (2008 ▶); Sztanke et al. (2008 ▶). For the preparation, see: Eweiss et al. (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Fun et al. (2008 ▶, 2009 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C10H12N4OS

M = 236.30

Orthorhombic,

a = 8.6908 (1) Å

b = 22.2551 (3) Å

c = 11.3771 (2) Å

V = 2200.50 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.28 mm−1

T = 100 K

0.58 × 0.29 × 0.27 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.855, T max = 0.929

41442 measured reflections

9726 independent reflections

9145 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.075

S = 1.01

9726 reflections

315 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 4628 Friedel pairs

Flack parameter: −0.02 (3)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809027275/ci2852sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027275/ci2852Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H12N4OS	F(000) = 992
Mr = 236.30	Dx = 1.427 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 9872 reflections
a = 8.6908 (1) Å	θ = 2.5–35.1°
b = 22.2551 (3) Å	µ = 0.28 mm−1
c = 11.3771 (2) Å	T = 100 K
V = 2200.50 (5) Å3	Block, colourless
Z = 8	0.58 × 0.29 × 0.27 mm

Bruker SMART APEXII CCD area-detector diffractometer	9726 independent reflections
Radiation source: fine-focus sealed tube	9145 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 35.2°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→14
Tmin = 0.855, Tmax = 0.929	k = −35→35
41442 measured reflections	l = −18→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.075	w = 1/[σ2(Fo2) + (0.0433P)2 + 0.2689P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.002
9726 reflections	Δρmax = 0.33 e Å−3
315 parameters	Δρmin = −0.19 e Å−3
1 restraint	Absolute structure: Flack (1983), 4628 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.02 (3)

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1A	0.08512 (3)	0.532701 (9)	0.19019 (2)	0.01524 (4)
O1A	0.33838 (9)	0.77054 (3)	−0.00794 (7)	0.01789 (13)
N1A	0.18273 (11)	0.70334 (3)	0.15180 (7)	0.01539 (14)
N2A	0.10587 (10)	0.65525 (3)	0.20140 (8)	0.01580 (14)
N3A	0.25603 (10)	0.61737 (3)	0.07393 (7)	0.01237 (13)
N4A	0.34200 (11)	0.57827 (3)	0.00333 (7)	0.01508 (14)
C1A	0.14799 (11)	0.60200 (4)	0.15681 (8)	0.01298 (14)
C2A	0.27309 (11)	0.67851 (4)	0.07402 (8)	0.01336 (15)
C3A	0.38198 (12)	0.70933 (4)	−0.00655 (9)	0.01540 (15)
H3AA	0.4868	0.7051	0.0215	0.018*
H3AB	0.3754	0.6923	−0.0849	0.018*
C4A	0.42434 (11)	0.80824 (4)	−0.07765 (9)	0.01387 (14)
C5A	0.53343 (13)	0.78880 (4)	−0.15850 (9)	0.01853 (17)
H5AA	0.5524	0.7480	−0.1685	0.022*
C6A	0.61434 (14)	0.83133 (5)	−0.22470 (10)	0.02183 (19)
H6AA	0.6870	0.8188	−0.2795	0.026*
C7A	0.58630 (13)	0.89233 (5)	−0.20862 (9)	0.02055 (19)
H7AA	0.6413	0.9207	−0.2516	0.025*
C8A	0.47564 (13)	0.91072 (4)	−0.12798 (9)	0.01740 (17)
H8AA	0.4571	0.9516	−0.1180	0.021*
C9A	0.39210 (11)	0.86951 (4)	−0.06189 (8)	0.01362 (15)
C10A	0.27083 (13)	0.88901 (4)	0.02363 (10)	0.01894 (18)
H10A	0.2761	0.9318	0.0340	0.028*
H10B	0.2875	0.8695	0.0978	0.028*
H10C	0.1712	0.8783	−0.0061	0.028*
S1B	0.89572 (3)	0.691199 (11)	0.41761 (2)	0.01782 (5)
O1B	0.57901 (9)	0.49790 (3)	0.17514 (7)	0.01652 (13)
N1B	0.53427 (11)	0.63533 (4)	0.24499 (8)	0.01717 (15)
N2B	0.63760 (11)	0.67783 (4)	0.28244 (8)	0.01748 (15)
N3B	0.71458 (10)	0.59546 (3)	0.35636 (7)	0.01283 (13)
N4B	0.79643 (11)	0.55068 (4)	0.41643 (9)	0.01770 (14)
C1B	0.74960 (12)	0.65567 (4)	0.35097 (8)	0.01391 (15)
C2B	0.58365 (11)	0.58530 (4)	0.29216 (8)	0.01315 (15)
C3B	0.50974 (11)	0.52552 (4)	0.27590 (8)	0.01388 (15)
H3BA	0.5256	0.5008	0.3450	0.017*
H3BB	0.3999	0.5302	0.2637	0.017*
C4B	0.53275 (11)	0.43946 (4)	0.15063 (8)	0.01406 (15)
C5B	0.40519 (12)	0.41259 (4)	0.20300 (9)	0.01678 (16)
H5BA	0.3470	0.4336	0.2579	0.020*
C6B	0.36530 (13)	0.35369 (4)	0.17238 (9)	0.01886 (18)
H6BA	0.2794	0.3357	0.2060	0.023*
C7B	0.45408 (14)	0.32217 (4)	0.09177 (9)	0.01915 (18)
H7BA	0.4287	0.2828	0.0723	0.023*
C8B	0.58097 (13)	0.34962 (4)	0.04025 (9)	0.01721 (17)
H8BA	0.6396	0.3281	−0.0137	0.021*
C9B	0.62274 (12)	0.40874 (4)	0.06744 (8)	0.01428 (15)
C10B	0.75914 (14)	0.43787 (5)	0.00943 (9)	0.02039 (18)
H10D	0.8209	0.4077	−0.0280	0.031*
H10E	0.8195	0.4584	0.0676	0.031*
H10F	0.7241	0.4662	−0.0483	0.031*
H1N4	0.281 (2)	0.5525 (8)	−0.0322 (16)	0.028 (4)*
H2N4	0.403 (2)	0.5622 (7)	0.0500 (16)	0.024 (4)*
H3N4	0.811 (2)	0.5664 (7)	0.4897 (18)	0.034 (4)*
H4N4	0.892 (2)	0.5482 (9)	0.3764 (18)	0.038 (5)*
H2N1	0.050 (2)	0.6623 (8)	0.2633 (17)	0.029 (4)*
H2N2	0.638 (2)	0.7148 (8)	0.2518 (16)	0.028 (4)*

	U11	U22	U33	U12	U13	U23
S1A	0.01653 (10)	0.01155 (8)	0.01764 (9)	−0.00295 (7)	0.00062 (8)	0.00233 (7)
O1A	0.0183 (3)	0.0099 (2)	0.0255 (3)	0.0003 (2)	0.0083 (3)	0.0032 (2)
N1A	0.0178 (4)	0.0107 (3)	0.0176 (3)	−0.0016 (3)	0.0030 (3)	0.0003 (2)
N2A	0.0175 (4)	0.0120 (3)	0.0179 (3)	−0.0015 (3)	0.0046 (3)	−0.0002 (3)
N3A	0.0128 (3)	0.0096 (3)	0.0147 (3)	−0.0002 (2)	0.0010 (3)	0.0000 (2)
N4A	0.0162 (4)	0.0122 (3)	0.0168 (3)	0.0013 (3)	0.0016 (3)	−0.0019 (2)
C1A	0.0129 (4)	0.0119 (3)	0.0141 (3)	−0.0011 (3)	−0.0001 (3)	0.0012 (3)
C2A	0.0146 (4)	0.0098 (3)	0.0156 (3)	−0.0012 (3)	0.0005 (3)	0.0006 (3)
C3A	0.0166 (4)	0.0099 (3)	0.0197 (4)	0.0000 (3)	0.0035 (3)	0.0013 (3)
C4A	0.0146 (4)	0.0114 (3)	0.0157 (3)	−0.0012 (3)	0.0016 (3)	0.0022 (3)
C5A	0.0207 (5)	0.0161 (4)	0.0188 (4)	0.0001 (3)	0.0055 (4)	0.0002 (3)
C6A	0.0237 (5)	0.0241 (4)	0.0176 (4)	−0.0014 (4)	0.0069 (4)	0.0033 (3)
C7A	0.0217 (5)	0.0220 (4)	0.0180 (4)	−0.0039 (4)	0.0027 (4)	0.0068 (3)
C8A	0.0193 (5)	0.0140 (3)	0.0189 (4)	−0.0024 (3)	−0.0007 (3)	0.0053 (3)
C9A	0.0135 (4)	0.0120 (3)	0.0153 (4)	−0.0004 (3)	−0.0009 (3)	0.0018 (3)
C10A	0.0184 (5)	0.0138 (3)	0.0246 (4)	0.0001 (3)	0.0047 (4)	−0.0004 (3)
S1B	0.01796 (11)	0.01668 (9)	0.01883 (10)	−0.00401 (8)	0.00217 (9)	−0.00556 (8)
O1B	0.0195 (3)	0.0124 (2)	0.0176 (3)	−0.0037 (2)	0.0050 (3)	−0.0036 (2)
N1B	0.0191 (4)	0.0138 (3)	0.0186 (3)	0.0014 (3)	−0.0034 (3)	−0.0004 (3)
N2B	0.0212 (4)	0.0110 (3)	0.0202 (3)	0.0016 (3)	−0.0026 (3)	−0.0004 (3)
N3B	0.0142 (4)	0.0101 (3)	0.0141 (3)	0.0004 (2)	−0.0005 (3)	−0.0001 (2)
N4B	0.0175 (4)	0.0150 (3)	0.0206 (3)	0.0016 (3)	−0.0039 (3)	0.0023 (3)
C1B	0.0168 (4)	0.0112 (3)	0.0137 (3)	−0.0004 (3)	0.0020 (3)	−0.0018 (3)
C2B	0.0136 (4)	0.0127 (3)	0.0131 (3)	0.0009 (3)	0.0001 (3)	−0.0012 (3)
C3B	0.0146 (4)	0.0129 (3)	0.0141 (3)	−0.0005 (3)	0.0012 (3)	−0.0009 (3)
C4B	0.0155 (4)	0.0115 (3)	0.0152 (3)	−0.0004 (3)	−0.0013 (3)	−0.0009 (3)
C5B	0.0169 (4)	0.0148 (3)	0.0186 (4)	−0.0018 (3)	0.0020 (3)	−0.0009 (3)
C6B	0.0194 (4)	0.0152 (3)	0.0220 (4)	−0.0033 (3)	−0.0005 (4)	0.0000 (3)
C7B	0.0235 (5)	0.0128 (3)	0.0212 (4)	−0.0021 (3)	−0.0032 (4)	−0.0010 (3)
C8B	0.0212 (5)	0.0142 (3)	0.0163 (4)	0.0013 (3)	−0.0028 (3)	−0.0027 (3)
C9B	0.0153 (4)	0.0143 (3)	0.0132 (3)	0.0009 (3)	−0.0007 (3)	−0.0011 (3)
C10B	0.0222 (5)	0.0212 (4)	0.0178 (4)	−0.0025 (4)	0.0049 (4)	−0.0027 (3)

S1A—C1A	1.6796 (9)	S1B—C1B	1.6771 (10)
O1A—C4A	1.3751 (11)	O1B—C4B	1.3895 (11)
O1A—C3A	1.4141 (11)	O1B—C3B	1.4334 (12)
N1A—C2A	1.3057 (12)	N1B—C2B	1.3086 (12)
N1A—N2A	1.3821 (11)	N1B—N2B	1.3720 (12)
N2A—C1A	1.3401 (12)	N2B—C1B	1.3412 (14)
N2A—H2N1	0.869 (19)	N2B—H2N2	0.894 (18)
N3A—C2A	1.3687 (11)	N3B—C2B	1.3709 (13)
N3A—C1A	1.3740 (12)	N3B—C1B	1.3754 (11)
N3A—N4A	1.4003 (11)	N3B—N4B	1.4023 (11)
N4A—H1N4	0.879 (18)	N4B—H3N4	0.91 (2)
N4A—H2N4	0.832 (18)	N4B—H4N4	0.95 (2)
C2A—C3A	1.4854 (13)	C2B—C3B	1.4888 (12)
C3A—H3AA	0.97	C3B—H3BA	0.97
C3A—H3AB	0.97	C3B—H3BB	0.97
C4A—C5A	1.3901 (14)	C4B—C5B	1.3935 (14)
C4A—C9A	1.4034 (12)	C4B—C9B	1.4054 (13)
C5A—C6A	1.3992 (14)	C5B—C6B	1.4000 (13)
C5A—H5AA	0.93	C5B—H5BA	0.93
C6A—C7A	1.3914 (16)	C6B—C7B	1.3886 (15)
C6A—H6AA	0.93	C6B—H6BA	0.93
C7A—C8A	1.3908 (16)	C7B—C8B	1.3903 (16)
C7A—H7AA	0.93	C7B—H7BA	0.93
C8A—C9A	1.3905 (13)	C8B—C9B	1.3994 (13)
C8A—H8AA	0.93	C8B—H8BA	0.93
C9A—C10A	1.4986 (14)	C9B—C10B	1.5037 (15)
C10A—H10A	0.96	C10B—H10D	0.96
C10A—H10B	0.96	C10B—H10E	0.96
C10A—H10C	0.96	C10B—H10F	0.96
C4A—O1A—C3A	116.66 (8)	C4B—O1B—C3B	116.13 (7)
C2A—N1A—N2A	103.87 (7)	C2B—N1B—N2B	104.16 (8)
C1A—N2A—N1A	113.47 (8)	C1B—N2B—N1B	113.71 (8)
C1A—N2A—H2N1	128.2 (12)	C1B—N2B—H2N2	124.2 (12)
N1A—N2A—H2N1	117.4 (12)	N1B—N2B—H2N2	121.1 (12)
C2A—N3A—C1A	108.73 (7)	C2B—N3B—C1B	108.71 (8)
C2A—N3A—N4A	124.09 (8)	C2B—N3B—N4B	124.29 (8)
C1A—N3A—N4A	127.12 (7)	C1B—N3B—N4B	127.00 (8)
N3A—N4A—H1N4	110.4 (12)	N3B—N4B—H3N4	104.0 (11)
N3A—N4A—H2N4	104.0 (12)	N3B—N4B—H4N4	104.5 (12)
H1N4—N4A—H2N4	113.4 (15)	H3N4—N4B—H4N4	110.0 (17)
N2A—C1A—N3A	103.07 (7)	N2B—C1B—N3B	102.92 (8)
N2A—C1A—S1A	129.61 (7)	N2B—C1B—S1B	129.71 (7)
N3A—C1A—S1A	127.31 (7)	N3B—C1B—S1B	127.36 (8)
N1A—C2A—N3A	110.86 (8)	N1B—C2B—N3B	110.50 (8)
N1A—C2A—C3A	127.30 (8)	N1B—C2B—C3B	124.61 (9)
N3A—C2A—C3A	121.84 (8)	N3B—C2B—C3B	124.88 (8)
O1A—C3A—C2A	106.32 (8)	O1B—C3B—C2B	107.54 (8)
O1A—C3A—H3AA	110.5	O1B—C3B—H3BA	110.2
C2A—C3A—H3AA	110.5	C2B—C3B—H3BA	110.2
O1A—C3A—H3AB	110.5	O1B—C3B—H3BB	110.2
C2A—C3A—H3AB	110.5	C2B—C3B—H3BB	110.2
H3AA—C3A—H3AB	108.7	H3BA—C3B—H3BB	108.5
O1A—C4A—C5A	124.21 (8)	O1B—C4B—C5B	123.10 (8)
O1A—C4A—C9A	114.25 (8)	O1B—C4B—C9B	115.43 (8)
C5A—C4A—C9A	121.54 (8)	C5B—C4B—C9B	121.46 (8)
C4A—C5A—C6A	119.23 (9)	C4B—C5B—C6B	119.51 (9)
C4A—C5A—H5AA	120.4	C4B—C5B—H5BA	120.2
C6A—C5A—H5AA	120.4	C6B—C5B—H5BA	120.2
C7A—C6A—C5A	120.08 (10)	C7B—C6B—C5B	119.98 (10)
C7A—C6A—H6AA	120.0	C7B—C6B—H6BA	120.0
C5A—C6A—H6AA	120.0	C5B—C6B—H6BA	120.0
C8A—C7A—C6A	119.67 (9)	C6B—C7B—C8B	119.82 (9)
C8A—C7A—H7AA	120.2	C6B—C7B—H7BA	120.1
C6A—C7A—H7AA	120.2	C8B—C7B—H7BA	120.1
C9A—C8A—C7A	121.58 (9)	C7B—C8B—C9B	121.72 (9)
C9A—C8A—H8AA	119.2	C7B—C8B—H8BA	119.1
C7A—C8A—H8AA	119.2	C9B—C8B—H8BA	119.1
C8A—C9A—C4A	117.87 (9)	C8B—C9B—C4B	117.51 (9)
C8A—C9A—C10A	121.82 (8)	C8B—C9B—C10B	120.86 (9)
C4A—C9A—C10A	120.31 (8)	C4B—C9B—C10B	121.64 (8)
C9A—C10A—H10A	109.5	C9B—C10B—H10D	109.5
C9A—C10A—H10B	109.5	C9B—C10B—H10E	109.5
H10A—C10A—H10B	109.5	H10D—C10B—H10E	109.5
C9A—C10A—H10C	109.5	C9B—C10B—H10F	109.5
H10A—C10A—H10C	109.5	H10D—C10B—H10F	109.5
H10B—C10A—H10C	109.5	H10E—C10B—H10F	109.5
C2A—N1A—N2A—C1A	0.60 (11)	C2B—N1B—N2B—C1B	0.20 (12)
N1A—N2A—C1A—N3A	−0.59 (11)	N1B—N2B—C1B—N3B	0.26 (11)
N1A—N2A—C1A—S1A	−179.77 (8)	N1B—N2B—C1B—S1B	−178.52 (8)
C2A—N3A—C1A—N2A	0.35 (10)	C2B—N3B—C1B—N2B	−0.61 (10)
N4A—N3A—C1A—N2A	177.58 (9)	N4B—N3B—C1B—N2B	179.33 (9)
C2A—N3A—C1A—S1A	179.56 (7)	C2B—N3B—C1B—S1B	178.21 (7)
N4A—N3A—C1A—S1A	−3.21 (14)	N4B—N3B—C1B—S1B	−1.85 (14)
N2A—N1A—C2A—N3A	−0.34 (11)	N2B—N1B—C2B—N3B	−0.59 (11)
N2A—N1A—C2A—C3A	179.47 (10)	N2B—N1B—C2B—C3B	−179.27 (9)
C1A—N3A—C2A—N1A	0.00 (11)	C1B—N3B—C2B—N1B	0.79 (11)
N4A—N3A—C2A—N1A	−177.34 (9)	N4B—N3B—C2B—N1B	−179.15 (9)
C1A—N3A—C2A—C3A	−179.83 (9)	C1B—N3B—C2B—C3B	179.47 (9)
N4A—N3A—C2A—C3A	2.84 (14)	N4B—N3B—C2B—C3B	−0.47 (14)
C4A—O1A—C3A—C2A	179.99 (8)	C4B—O1B—C3B—C2B	175.45 (8)
N1A—C2A—C3A—O1A	−16.61 (14)	N1B—C2B—C3B—O1B	90.26 (11)
N3A—C2A—C3A—O1A	163.18 (9)	N3B—C2B—C3B—O1B	−88.24 (11)
C3A—O1A—C4A—C5A	10.15 (15)	C3B—O1B—C4B—C5B	13.09 (13)
C3A—O1A—C4A—C9A	−170.52 (9)	C3B—O1B—C4B—C9B	−167.61 (8)
O1A—C4A—C5A—C6A	−179.92 (10)	O1B—C4B—C5B—C6B	179.26 (9)
C9A—C4A—C5A—C6A	0.80 (16)	C9B—C4B—C5B—C6B	0.00 (15)
C4A—C5A—C6A—C7A	0.55 (17)	C4B—C5B—C6B—C7B	1.03 (16)
C5A—C6A—C7A—C8A	−1.12 (17)	C5B—C6B—C7B—C8B	−1.06 (16)
C6A—C7A—C8A—C9A	0.37 (17)	C6B—C7B—C8B—C9B	0.06 (16)
C7A—C8A—C9A—C4A	0.93 (15)	C7B—C8B—C9B—C4B	0.93 (14)
C7A—C8A—C9A—C10A	−178.93 (10)	C7B—C8B—C9B—C10B	−179.14 (10)
O1A—C4A—C9A—C8A	179.13 (9)	O1B—C4B—C9B—C8B	179.73 (9)
C5A—C4A—C9A—C8A	−1.52 (15)	C5B—C4B—C9B—C8B	−0.96 (14)
O1A—C4A—C9A—C10A	−1.01 (13)	O1B—C4B—C9B—C10B	−0.20 (13)
C5A—C4A—C9A—C10A	178.34 (10)	C5B—C4B—C9B—C10B	179.11 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N4A—H1N4···N4Bi	0.88 (2)	2.46 (2)	3.2651 (12)	152 (2)
N4A—H2N4···O1B	0.83 (2)	2.53 (2)	3.3560 (11)	171 (2)
N4B—H4N4···S1Aii	0.95 (2)	2.72 (2)	3.6167 (10)	157 (2)
N2A—H2N1···S1Biii	0.87 (2)	2.30 (2)	3.1665 (9)	174 (2)
N2B—H2N2···N1Aiv	0.89 (2)	2.18 (2)	3.0589 (11)	166 (2)
C8A—H8AA···S1Av	0.93	2.86	3.4537 (10)	123
C3B—H3BB···S1A	0.97	2.86	3.8203 (10)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4A—H1N4⋯N4Bi	0.88 (2)	2.46 (2)	3.2651 (12)	152 (2)
N4A—H2N4⋯O1B	0.83 (2)	2.53 (2)	3.3560 (11)	171 (2)
N4B—H4N4⋯S1Aii	0.95 (2)	2.72 (2)	3.6167 (10)	157 (2)
N2A—H2N1⋯S1Biii	0.87 (2)	2.30 (2)	3.1665 (9)	174 (2)
N2B—H2N2⋯N1Aiv	0.89 (2)	2.18 (2)	3.0589 (11)	166 (2)
C8A—H8AA⋯S1Av	0.93	2.86	3.4537 (10)	123
C3B—H3BB⋯S1A	0.97	2.86	3.8203 (10)	170

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .